One-Pot Synthesis of Benzoazole-Substituted Thioenamines via a Cross Dehydrogenation Coupling (CDC) Reaction.

An iodine-catalyzed synthesis of benzoazole-substituted thioenamines in a one-pot manner was reported. Using 2-aminothiophenols (or 2-aminophenols or 1,2-phenylenediamines), tetramethylthiuram disulfide (TMTD), and enamines (mainly indoles) as starting materials, the target C(sp 2 )-S formation products (benzoazole-substituted thioenamines) could be furnished smoothly in good yields. The reaction might proceed through an electrophilic substitution pathway in a cross dehydrogenation coupling (CDC) manner. The protocol is metal-free and features easy performance, a one-pot manner, a good functional group tolerance, and good yields.